EP2785307A1 - Composition dentaire autoadhésive à un composant, son procédé de fabrication et son utilisation - Google Patents
Composition dentaire autoadhésive à un composant, son procédé de fabrication et son utilisationInfo
- Publication number
- EP2785307A1 EP2785307A1 EP12798129.8A EP12798129A EP2785307A1 EP 2785307 A1 EP2785307 A1 EP 2785307A1 EP 12798129 A EP12798129 A EP 12798129A EP 2785307 A1 EP2785307 A1 EP 2785307A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- component
- composition
- copper
- meth
- composition according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 189
- 239000000853 adhesive Substances 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 6
- 230000008569 process Effects 0.000 title description 6
- 239000000945 filler Substances 0.000 claims abstract description 54
- 230000002378 acidificating effect Effects 0.000 claims abstract description 20
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims abstract description 17
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 17
- 150000003624 transition metals Chemical class 0.000 claims abstract description 16
- 239000000654 additive Substances 0.000 claims abstract description 12
- 239000007800 oxidant agent Substances 0.000 claims abstract description 11
- 230000000996 additive effect Effects 0.000 claims abstract 2
- -1 copper carboxylates Chemical class 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 20
- 239000000178 monomer Substances 0.000 claims description 20
- 210000004268 dentin Anatomy 0.000 claims description 18
- 239000010949 copper Substances 0.000 claims description 17
- 229910052802 copper Inorganic materials 0.000 claims description 15
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 13
- 230000001070 adhesive effect Effects 0.000 claims description 13
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 11
- 210000003298 dental enamel Anatomy 0.000 claims description 11
- 238000005530 etching Methods 0.000 claims description 11
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000004568 cement Substances 0.000 claims description 5
- 150000001879 copper Chemical class 0.000 claims description 5
- 238000011049 filling Methods 0.000 claims description 5
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical group [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 claims description 5
- 229920001223 polyethylene glycol Polymers 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- YEOCHZFPBYUXMC-UHFFFAOYSA-L copper benzoate Chemical compound [Cu+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 YEOCHZFPBYUXMC-UHFFFAOYSA-L 0.000 claims description 4
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 230000005855 radiation Effects 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical group O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical group O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 230000009969 flowable effect Effects 0.000 claims description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000626 sulfinic acid group Chemical group 0.000 claims description 3
- 238000010998 test method Methods 0.000 claims description 3
- 150000003568 thioethers Chemical class 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 239000008199 coating composition Substances 0.000 claims description 2
- 229940120693 copper naphthenate Drugs 0.000 claims description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 2
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 claims description 2
- ZKXWKVVCCTZOLD-UHFFFAOYSA-N copper;4-hydroxypent-3-en-2-one Chemical compound [Cu].CC(O)=CC(C)=O.CC(O)=CC(C)=O ZKXWKVVCCTZOLD-UHFFFAOYSA-N 0.000 claims description 2
- 239000011162 core material Substances 0.000 claims description 2
- 210000004262 dental pulp cavity Anatomy 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 239000002631 root canal filling material Substances 0.000 claims description 2
- 125000006850 spacer group Chemical group 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 150000007970 thio esters Chemical class 0.000 claims description 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 49
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
- 239000002253 acid Substances 0.000 description 24
- 239000005548 dental material Substances 0.000 description 17
- 239000000126 substance Substances 0.000 description 17
- 239000002245 particle Substances 0.000 description 16
- 239000011347 resin Substances 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- 238000009472 formulation Methods 0.000 description 13
- 229910019142 PO4 Inorganic materials 0.000 description 11
- OXHDYFKENBXUEM-UHFFFAOYSA-N glyphosine Chemical compound OC(=O)CN(CP(O)(O)=O)CP(O)(O)=O OXHDYFKENBXUEM-UHFFFAOYSA-N 0.000 description 11
- 239000010452 phosphate Substances 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000000975 dye Substances 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
- 238000003860 storage Methods 0.000 description 9
- 239000002131 composite material Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000011159 matrix material Substances 0.000 description 7
- 239000002105 nanoparticle Substances 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- 239000007767 bonding agent Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229910003439 heavy metal oxide Inorganic materials 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229910001512 metal fluoride Inorganic materials 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 4
- UEKHZPDUBLCUHN-UHFFFAOYSA-N 2-[[3,5,5-trimethyl-6-[2-(2-methylprop-2-enoyloxy)ethoxycarbonylamino]hexyl]carbamoyloxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(=O)NCCC(C)CC(C)(C)CNC(=O)OCCOC(=O)C(C)=C UEKHZPDUBLCUHN-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000005749 Copper compound Substances 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 229930006711 bornane-2,3-dione Natural products 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 150000001880 copper compounds Chemical class 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000003479 dental cement Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 4
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 210000000988 bone and bone Anatomy 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000011350 dental composite resin Substances 0.000 description 3
- 230000001627 detrimental effect Effects 0.000 description 3
- 229960001484 edetic acid Drugs 0.000 description 3
- 150000002222 fluorine compounds Chemical class 0.000 description 3
- 229910021485 fumed silica Inorganic materials 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 238000002203 pretreatment Methods 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 229910052712 strontium Inorganic materials 0.000 description 3
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000012756 surface treatment agent Substances 0.000 description 3
- 238000004627 transmission electron microscopy Methods 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 description 2
- FJPGAMCQJNLTJC-UHFFFAOYSA-N 2,3-Heptanedione Chemical compound CCCCC(=O)C(C)=O FJPGAMCQJNLTJC-UHFFFAOYSA-N 0.000 description 2
- XCBBNTFYSLADTO-UHFFFAOYSA-N 2,3-Octanedione Chemical compound CCCCCC(=O)C(C)=O XCBBNTFYSLADTO-UHFFFAOYSA-N 0.000 description 2
- IBDVWXAVKPRHCU-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)C(C)=C IBDVWXAVKPRHCU-UHFFFAOYSA-N 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- LBCCPKFTHIBIKU-UHFFFAOYSA-N 3,4-Heptanedione Chemical compound CCCC(=O)C(=O)CC LBCCPKFTHIBIKU-UHFFFAOYSA-N 0.000 description 2
- KVFQMAZOBTXCAZ-UHFFFAOYSA-N 3,4-Hexanedione Chemical compound CCC(=O)C(=O)CC KVFQMAZOBTXCAZ-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-N 0.000 description 2
- CDSULTPOCMWJCM-UHFFFAOYSA-N 4h-chromene-2,3-dione Chemical class C1=CC=C2OC(=O)C(=O)CC2=C1 CDSULTPOCMWJCM-UHFFFAOYSA-N 0.000 description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- XYZZKVRWGOWVGO-UHFFFAOYSA-N Glycerol-phosphate Chemical compound OP(O)(O)=O.OCC(O)CO XYZZKVRWGOWVGO-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
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- XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-N 0.000 description 1
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- 239000012991 xanthate Substances 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
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- 229940075624 ytterbium oxide Drugs 0.000 description 1
- XASAPYQVQBKMIN-UHFFFAOYSA-K ytterbium(iii) fluoride Chemical compound F[Yb](F)F XASAPYQVQBKMIN-UHFFFAOYSA-K 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- RBORBHYCVONNJH-UHFFFAOYSA-K yttrium(iii) fluoride Chemical compound F[Y](F)F RBORBHYCVONNJH-UHFFFAOYSA-K 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
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- SXPUVBFQXJHYNS-UHFFFAOYSA-N α-furil Chemical compound C=1C=COC=1C(=O)C(=O)C1=CC=CO1 SXPUVBFQXJHYNS-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/50—Preparations specially adapted for dental root treatment
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/10—Homopolymers or copolymers of methacrylic acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
- A61C19/00—Dental auxiliary appliances
- A61C19/003—Apparatus for curing resins by radiation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/15—Compositions characterised by their physical properties
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
- A61K6/62—Photochemical radical initiators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/70—Preparations for dentistry comprising inorganic additives
- A61K6/71—Fillers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
Definitions
- the invention relates to a one-component self-adhesive dental composition
- a photoinitiator system comprising a photoinitiator system, an oxidizing agent and a copper compound.
- the composition can be used for various dental applications.
- Dental composites are well known in dentistry and are widely used as restorative materials (filling composites) or as cements (resin cements) in the prosthodontic field.
- Generally composites are hydrophobic in nature and contain as main parts of the formulation inorganic fillers, a (meth)acrylate based resin matrix and initiators for the radical polymerization.
- composites typically require a pre-treatment of the tooth surface by using a bonding agent or a bonding system. This may result in a rather complex and time consuming procedure. Therefore attempts were made to develop self-adhesive composites which avoid the use of an additional bonding agent/system resulting in materials which are easier and faster to use for the dentist.
- Two-component systems are not always easy to apply and use. Thus, it is generally desirable to have a one-component system.
- EP 2 153 81 1 A2 (Kerr) relates to a single-part, light-curable, self-adhering dental restorative composition comprising three different polymerizable monomers, a photo-initiator and one or more fillers.
- compositions are self-adhesive compositions. If the composition is cured by photopolymerization it is possible to formulate one-component systems. If the composition comprises a redox initiator system comprising e.g. an organic peroxide and activator then for reasons of storage stability peroxide and activator are present in spatially separated parts. In a particular example a composition is described with an initiator system, which can comprise sodium toluene sulfinate, sodium peroxodisulfate, a barbituric acid derivative and copper acetate.
- an initiator system which can comprise sodium toluene sulfinate, sodium peroxodisulfate, a barbituric acid derivative and copper acetate.
- JP 201 1-121869 relates to a chemical polymerization catalyst composition for dental curable materials comprising an aryl borate compound, acidic compound, inorganic peroxide and bivalent copper compound.
- the system is formulated as a two-component system.
- a further embodiment of the invention is directed to a process of producing the composition as described in any of the preceding claims comprising the steps of mixing and/or kneading.
- a composition can be classified as "storage stable", if it remains stable over a considerable long period of time (at least about 4 weeks to more than about 12 months under ambient conditions).
- a storage stable composition does typically not show decomposition of the components contained therein or premature polymerization over time. Moreover, the features intended to be achieved by the composition shall not diminish more than desired.
- “One component” means that all of the components mentioned are present in the composition during storage and use. That is, the composition to be applied or used is not prepared by mixing different parts of the composition before use. In contrast to one-component compositions, those compositions are often referred to as two-component compositions (e.g. being formulated as powder/liquid, liquid/liquid or paste/paste compositions).
- a “dental composition” or a “composition for dental use” or a “composition to be used in the dental field” is any composition which can be used in the dental field. In this respect the composition should be not detrimental to the patients ' health and thus free of hazardous and toxic components being able to migrate out of the composition.
- dental compositions include permanent and temporary crown and bridge materials, artificial crowns, anterior or posterior filling materials, adhesives, mill blanks, lab materials and orthodontic devices.
- Dental compositions are typically hardenable compositions, which can be hardened at ambient conditions, including a temperature range from about 15 to 50°C or from about 20 to 40°C within a time frame of about 30 min or 20 min or 10 min.
- Dental compositions are typically provided to the practitioner in comparable small volumes, that is volumes in the range from about 0.1 to about 100 ml or from about 0.5 to about 50 ml or from about 1 to about 30 ml. Thus, the storage volume of useful packaging devices is within these ranges.
- a "monomer” is any chemical substance which can be characterized by a chemical formula, bearing polymerizable groups (including (meth)acrylate groups) which can be polymerized to oligomers or polymers thereby increasing the molecular weight.
- the molecular weight of monomers can usually simply be calculated based on the chemical formula given.
- a “hardenable component or material” or “polymerizable component” is any component which can be cured or solidified e.g. by heating to cause polymerization, chemical crosslinking, radiation-induced polymerization or crosslinking by using a redox initiator.
- a hardenable component may contain only one, two, three or more polymerizable groups. Typical examples of polymerizable groups include unsaturated carbon groups, such as a vinyl group being present i.a. in a (methyl)acrylate group.
- An “ethylenically unsaturated acidic compound” is meant to include monomers, oligomers, and polymers having ethylenic unsaturation and acid and/or acid-precursor functionality.
- Acidic- precursor functionalities include, e.g. anhydrides, acid halides and pyrophosphates.
- the acidic group preferably comprises one or more carboxylic acid residues, such as -COOH or -CO-O- CO-, phosphoric acid residues, such as -0-P(0)(OH)OH, phosphonic acid residues such as C- P(0)(OH)OH, sulfonic acid residues, such as -S0 3 H or sulfinic acid residues such as -S0 2 H.
- a "filler” contains all fillers being present in the hardenable composition. Only one type of filler or a mixture of different fillers can be used.
- a "non-surface treated filler” is a filler having a surface which has not been exposed to reactive substances resulting in a modification of the surface of the filler to make the filler more compatible or reactive with other components of the composition.
- dental adhesive refers to a composition used as a pre-treatment on a dental structure (e. g., a tooth) to adhere a "dental material” (e. g., “restorative” an orthodontic appliance (e. g., bracket), or an “orthodontic adhesive”) to a dental surface.
- a "dental material” e. g., "restorative” an orthodontic appliance (e. g., bracket), or an “orthodontic adhesive”
- an “orthodontic adhesive” refers to a composition used to adhere an orthodontic appliance to a dental (e. g., tooth) surface.
- the dental surface is pre-treated, e. g., by etching, priming, and/or applying an adhesive to enhance the adhesion of the "orthodontic adhesive" to the dental surface.
- tooth surface refers to the surface of tooth structures (e. g., enamel, dentin, and cementum) and bone.
- a self-etching composition refers to a composition which bonds to a dental surface without pre-treating the dental surface with an etchant.
- a self-etching composition can also function as a self-primer wherein no separate etchant or primer is used.
- a self-adhesive composition refers to a composition that is capable of bonding to a dental surface without pre-treating the dental surface with a primer or bonding agent.
- a self-adhesive composition is also a self-etching composition wherein no separate etchant is used.
- an "untreated" dental surface refers to a tooth or bone surface that has not been treated with an etchant, primer, or bonding agent prior to application of a self-etching adhesive or a self-adhesive composition.
- an "unetched" dental surface refers to a tooth or bone surface that has not been treated with an etchant prior to application of a self-etching adhesive or a self-adhesive composition of the present invention.
- an “etchant” refers to an acidic composition that is capable of fully or partially solubilizing (i. e., etching) a dental surface.
- the etching effect can be visible to the naked human eye and/or instrumentally detectably (e. g., by light microscopy).
- an etchant is applied to the dental structure surface for a period of about 10 to 30 seconds.
- (meth) acryl is a shorthand term referring to "acryl” and/or "methacryl".
- a "nano-sized filler” is a filler, the individual particles thereof have a size in the region of nanometers, e.g. an average particle diameter of less than about 200 nm. Useful examples are given in US 6,899,948 and US 6,572,693, the content of which especially with regard to nano- sized silica particles is herein incorporated by reference.
- an “initiator or initiator system” is a substance being able to start the curing process of a hardenable compound.
- a “curing, hardening or setting reaction” is used interchangeable and refers to a reaction wherein physical properties such as viscosity and hardness of a composition changes over the time due to a chemical reaction between the individual components.
- a “derivative” is a chemical compound showing a chemical structure closely related to the corresponding reference compound and containing all featured structural elements of the corresponding reference compound but having small modifications like bearing in addition comparably small additional chemical groups like e.g. CH 3 , Br, CI, or F or not bearing comparably small chemical groups like e.g. CH 3 in comparison to the corresponding reference compound.
- the following examples might illustrate this: tetramethyl bis-phenol A bearing four additional methyl groups with respect to the reference compound bis-phenol A, and bis-phenol F not bearing two additional methyl groups with respect to the reference compound bis-phenol A are derivatives of bis-phenol A within the meaning of this definition.
- visible light is used to refer to light having a wavelength of about 400 to about 800 nanometers (nm).
- Ambient conditions mean the conditions which the inventive composition is usually subjected to during storage and handling.
- Ambient conditions may, for example, be a pressure of about 900 to about 1 100 mbar, a temperature of about -10 to about 60 °C and a relative humidity of about 10 to about 100 %.
- ambient conditions are adjusted to about 23 °C and about 1013 mbar.
- ambient conditions are reasonably understood as a pressure of about 950 to about 1050 mbar, temperature of about 15 to about 40 °C and relative humidity of about 20 to about 80%.
- the inventive composition is suitable to solve at least one of the above mentioned objectives e.g. providing a one-component, self-adhesive dental composition with good adhesive properties especially with respect to dentin surfaces.
- the composition is self-adhesive. That is, the composition adheres to dental surfaces without a pre-treatment using e.g. an etchant and/or a bonding system.
- composition as a one-component dental formulation facilitates the application by the practitioner during use.
- the composition can be applied as it is, using common equipment already present in the dental office.
- composition shows good adhesion performance both to enamel and dentin without the use of a bonding agent or a bonding system.
- composition typically has overall good mechanical and aesthetic properties.
- adhesion to dentin determined according to wire loop adhesion (see experimental part): at least about 5 MPa or at least about 7 or at least about 9 MPa,
- adhesion to enamel determined according to wire loop adhesion (see experimental part): at least about 7 MPa or at least about 9 or at least about 1 1 MPa,
- the viscosity of the composition is typically adjusted.
- suitable viscosities include e.g. from about 1 to about 150 Pa * s or from about 10 to about 120 Pa * s (23°C; shear rate: 100 1/s).
- the viscosity can be determined as follows: The viscosity can be measured using a Physica MCR 301 Rheometer (Anton Paar, Graz, Austria) with a cone/plate geometry CP25-1 under controlled shear rate at 23 °C. The diameter is 25 mm, the cone angle 1 °, and the separation between the cone tip and the plate 49 ⁇ . The shear rate is ramped down logarithmically from 1000 s "1 to 1 s "1 , with a total of 23 data points being collected. The integration time for each data point was 10 s.
- the invention provides a composition which can be hardened in an acceptable time frame, e.g., less than about 300 seconds (s) or less than about 180 s or less than about 120 s, and to a sufficient depth using visible light source equipment already available in the dental office or electronics fabrication facilities.
- an acceptable time frame e.g., less than about 300 seconds (s) or less than about 180 s or less than about 120 s, and to a sufficient depth using visible light source equipment already available in the dental office or electronics fabrication facilities.
- the inventive composition if dissolved or dispersed in water (e.g. 1 g in 10 ml) typically shows a pH value in the range from about 0 to about 5 or from about 1 to about 4. That is, the composition as a whole is acidic.
- the inventive composition comprises one or more radically polymerizable components with acid moiety as component (A) or part of component (A).
- Mw Molecular weight
- Viscosity from about 0.1 to about 10 Pa * s, or from about 0.2 to about 5 Pa * s or from about 0.5 to about 2 Pa * s measured at 23°C, and/or
- Refractive index from about 1 .42 to about 1 .55 (nD).
- component (A) with at least one of the following features can be preferred, especially, if the hardenable composition should show sufficient adhesiveness:
- molecular weight being in the range from about 70 to about 700 or from about 100 to about 600 or from about 200 to about 500 g/mol.
- the ethylenically unsaturated acidic compound can typically be represented by formula (I)
- A being an ethylenically unsaturated group, such as a (meth)acryl moiety
- B being a spacer group, such as (i) linear or branched C1 to C12 alkyl, optionally substituted with other functional groups (e.g. halogenides, OH or mixtures thereof)
- C6 to C12 aryl optionally substituted with other functional groups (e.g. halogenides, OH or mixtures thereof)
- organic group having 4 to 20 carbon atoms bonded to one another by one or more ether, thioether, ester, thioester, thiocarbonyl, amide, urethane, carbonyl and/or sulfonyl linkages, and
- the acidic group comprises one or more carboxylic acid residues, such as -COOH or - CO-0-CO-, phosphoric acid residues, such as -0-P(0)(OH)OH, phosphonic acid residues, such as C-P(0)(OH)(OH), sulphonic acid residues, such as -S0 3 H or sulfinic acid residues such as -S0 2 H.
- carboxylic acid residues such as -COOH or - CO-0-CO-
- phosphoric acid residues such as -0-P(0)(OH)OH
- phosphonic acid residues such as C-P(0)(OH)(OH)
- sulphonic acid residues such as -S0 3 H or sulfinic acid residues such as -S0 2 H.
- ethylenically unsaturated acidic compounds as component (A) include, but are not limited to glycerol phosphate mono(meth)acrylate, glycerol phosphate di(meth)acrylate, hydroxyethyl (meth)acrylate (e.g., HEMA) phosphate, bis((meth)acryloxyethyl) phosphate, (meth)acryloxypropyl phosphate, bis((meth)acryloxypropyl) phosphate, bis((meth)acryloxy)propyloxy phosphate, (meth)acryloxyhexyl phosphate, bis((meth)acryloxyhexyl) phosphate, (meth)acryloxyoctyl phosphate, bis((meth)acryloxyoctyl) phosphate, (meth)acryloxydecyl phosphate, bis((meth)acryloxydecyl) phosphate, caprolactone methacrylate phosphate,
- Some of these compounds can be obtained, e.g., as reaction products between isocyanatoalkyl (meth)acrylates and carboxylic acids. Additional compounds of this type having both acid- functional and ethylenically unsaturated components are described in US 4,872,936 (Engelbrecht) and US 5,130,347 (Mitra). A wide variety of such compounds containing both the ethylenically unsaturated and acid moieties can be used. If desired, mixtures of such compounds can be used.
- ethylenically unsaturated compounds with acid moiety include, for example, polymerizable bisphosphonic acids; AA:ITA:IEM (copolymer of acrylic acid:itaconic acid with pendent methacrylate made by reacting AA:ITA copolymer with sufficient 2-isocyanatoethyl methacrylate to convert a portion of the acid groups of the copolymer to pendent methacrylate groups as described, e.g.
- Example 1 1 of US 5, 130,347 (Mitra)); and those recited in US 4,259,075 (Yamauchi et al.), US 4,499,251 (Omura et al.), US 4,537,940 (Omura et al.), US 4,539,382 (Omura et al.), US 5,530,038 (Yamamoto et al.), US 6,458,868 (Okada et al.), and EP 0 712 622 A1 (Tokuyama Corp.) and EP 1 051 961 A1 (Kuraray Co., Ltd.).
- the unsaturated acidic compound can be present in the composition in an amount of at least about 3 or at least about 5 or at least about 10 wt.-%, wt.-% with respect to the weight of the whole composition.
- amounts of up to about 80 or up to about 70 or up to about 60 wt.-% can still be useful, wt.-% with respect to the weight of the whole composition.
- Useful amounts include from about 3 to about 80 or from about 5 to about 70 or from about 10 to about 60 wt.-% with respect to the weight of the whole composition.
- the inventive composition comprises one or more radically polymerizable component(s) without acid moiety as component (B) or as part of component (B).
- This component is typically a free-radically polymerizable material, including ethylenically unsaturated monomer, monomers or oligomers or polymers.
- Component (B) may also comprise a hydroxyl group, a 1 ,3-diketo moiety or both.
- Such polymerizable materials include mono-, di- or poly-acrylates and methacrylates such as methyl acrylate, methyl methacrylate, ethyl (meth)acrylate, isopropyl (meth)acrylate, n-hexyl (meth)acrylate, stearyl (meth)acrylate, allyl (meth)acrylate, glycerol di(meth)acrylate, the diurethane dimethacrylate called UDMA (mixture of isomers, e.g.
- Rohm Plex 6661-0 being the reaction product of 2-hydroxyethyl methacrylate (HEMA) and 2,2,4-trimethylhexamethylene diisocyanate (TMDI), glycerol tri(meth)acrylate, ethyleneglycol di(meth)acrylate, diethyleneglycol di(meth)acrylate, triethyleneglycol di(meth)acrylate, 1 ,3-propanediol diacrylate, 1 ,3-propanediol dimethacrylate, trimethylolpropane tri(meth)acrylate, 1 ,2,4-butanetriol tri(meth)acrylate, 1 ,4- cyclohexanediol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, sorbitol hexa(meth)
- Further polymerizable components are di(meth)acrylates of ethoxylated bis-phenol A, for example 2,2'-bis(4-(meth)acryloxytetraethoxyphenyl)propanes, urethane (meth)acrylates and (meth)acrylamides.
- the monomers used can furthermore be esters of [alpha]-cyanoacrylic acid, crotonic acid, cinnamic acid and sorbic acid.
- methacrylic esters mentioned in EP 0 235 826 such as bis[3[4]- methacryl-oxymethyl-8(9)-tricyclo[5.2.1.0 2,6 ]decylmethyl triglycolate.
- Suitable are also 2,2-bis- 4(3-methacryloxy-2-hydroxypropoxy)phenylpropane (Bis-GMA), 2,2-bis-4(3-methacryl- oxypropoxy)phenylpropane, 7,7,9-trimethyl-4, 13-dioxo-3, 14-dioxa-5, 12-diazahexadecane-1 , 16- dioxy dimethacrylate (UDMA), urethane (meth)acrylates and di(meth)acrylates of bishydroxymethyltricyclo-(5.2.1 .0 2,6 )decane.
- Bis-GMA 2,2-bis- 4(3-methacryloxy-2-hydroxypropoxy)phenylpropane
- UDMA 16- dioxy dimethacrylate
- urethane (meth)acrylates and di(meth)acrylates of bishydroxymethyltricyclo-(5.2.1 .0 2,6 )decane 2,2-bis- 4(3-methacryloxy-2-hydroxypropoxy
- ethylenically unsaturated monomers can be employed in the dental composition(s) either alone or in combination with the other ethylenically unsaturated monomers.
- hardenable components which can be added include oligomeric or polymeric compounds, such as polyester urethane (meth)acrylates, polyether urethane (meth)acrylates, polycarbonate urethane (meth)acrylates and poly(meth)acrylate urethane (meth)acrylates.
- the molecular weight of these compounds is typically less than 20,000 g/mol, particularly less than 15,000 g/mol and in particular less than 10,000 g/mol.
- component (B) or part of component (B) can sometime be preferred.
- Adding these components may facilitate the production process.
- polymerizable monomers examples include: polymerizable monomers, oligomers or polymers containing a hydroxide group and a polymerizable unsaturated group such as an acryloyl group, a methacryloyi group, a vinyl group or an allyl group and the like. Monomers are particularly preferable.
- HEMA 2-hydroxyethyl (meth)acrylate
- 2- or 3- hydroxypropyl (meth)acrylate 4-hydroxybutyl (meth)acrylate, 5-hydroxypentyl (meth)acrylate, 6- hydroxyhexyl (meth)acrylate, 10-hydroxydecyl (meth)acrylate
- dialkylene glycol mono(meth)acrylate for example, diethylene glycol mono(meth)acrylate, triethylene glycol mono(meth)acrylate, tetraethylene glycol mono(meth)acrylate, polyethylene glycol mono(meth)acrylate, dipropylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate, and further 1 ,2- or 1 ,3- and 2,3-dihydroxypropyl (meth)acrylate, 2- hydroxypropyl-1 ,3-di(meth)acrylate, 3-hydroxypropyl-1 ,2-di(meth)acrylate, N-(meth)acryl
- AAEMA acetoacetoxy ethylmethacrylate
- component (B) comprises mixtures of unsaturated hydroxyl- and/or 1 ,3-diketo functional compounds (e.g. HEMA and/or AA-EMA) with unsaturated compounds not having these functionalities.
- Component (B) is typically present in the composition in an amount of at least about 5 wt.-% or at least about 10 wt.-% or at least about 20 wt.-% with respect to the weight of the whole composition.
- the amount of component (B) contained in the composition is typically up to about 65 wt.-% or up to about 55 wt.-% or up to about 45 wt.-% with respect to the weight of the whole composition.
- Typical ranges include from about 5 to about 65 or from about 10 to about 55 or from about 20 to about 45 or wt.-% with respect to the weight of the whole composition.
- the composition comprises an oxidizing agent as component (C) or part of component (C).
- the oxidizing agent is selected from persulfate(s) or mixtures thereof.
- the oxidizing agent should be sufficiently stable in order to be compounded into a dental composition.
- the oxidizing agent does typically not contain organic residues, e.g. carbon- carbon moieties and such can be characterized as an inorganic substance.
- the persulfate or its radicals which may be produced during the hardening reaction is water-soluble.
- Water-soluble means that the persulfate can be dissolved in water, e.g. by dissociating into ions.
- D being selected from Li, Na, K, NH 4 , NR 4 , with R being selected from H and CH 3 .
- persulfate(s) examples include, Na 2 S 2 0 8 , K 2 S 2 0 8 , (NH 4 ) 2 S 2 0 8 and mixtures thereof.
- the amount of persulfate which can be used is not particularly limited.
- the persulfate should be used in an amount sufficient to achieve the intended purpose.
- Useful amounts include: • at least about 0.1 wt.-% or at least about 0.3 wt.-% or at least about 0.5 wt.-% with respect to the whole composition and/or
- Typical ranges include from about 0.1 wt.-% to about 10 wt.-% or from about from about 0.3 wt- % to about 5 wt.-% or from about 0.5 wt.-% to about 2 wt.-% with respect to the whole composition.
- the persulfate can be pre-mixed with filler particles and added to the remaining components of the composition during production.
- the inventive composition comprises one or more transition metal component(s) as component (D) or part of component (D).
- Suitable transition metal component(s) include organic and/or inorganic salt(s) from titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper and/or zinc.
- Useful salts include acetate(s), chloride(s), sulphate(s), benzoate(s), acetylacetonate(s), naphthenate(s), carboxylate(s), bis(1-phenylpentan-1 ,3-dione) complexes, salicylate(s), complexes with ethylenediaminetetraacetic acid of either of the transition metals and mixtures thereof.
- the transition metal component is in an oxidation stage, which allows the component to be reduced.
- Useful oxidation stages include +2, +3, +4, +5, +6 and +7, as applicable.
- Copper component(s) are sometimes preferred.
- the oxidation stage of copper in the copper component(s) is preferably +1 or +2.
- Typical examples of copper component(s) which can be used include salts and complexes of copper including copper acetate, copper chloride, copper benzoate, copper acetylacetonate, copper naphthenate, copper carboxylates, copper bis(1-phenylpentan-1 ,3-dione) complex (copper procetonate), , copper salicylate, complexes of copper with thiourea, ethylenediaminetetraacetic acid and/or mixtures thereof.
- the copper compounds can be used in hyd rated form or free of water.
- transition metal component which can be used is not particularly limited.
- the transition metal salt should be used in an amount sufficient to achieve the intended purpose.
- the transition metal component is typically present in the composition in an amount of at least about 0.0001 wt.-% or at least about 0.001 wt.-% or at least about 0.01 wt.-%.
- the amount of transition metal component contained in the composition is typically up to about 3 wt.-% or up to about 2 wt.-% or up to about 1.8 wt.-%.
- Typical ranges include from about 0.0001 to about 3 or from about 0.001 to about 2 or from about 0.01 to about 1.8 wt.-%.
- the inventive composition comprises one or more photoinitiator systems as component (E) or part of component (E).
- photoinitiator systems can include more than one component.
- a class of initiators capable of initiating polymerization of free radically active functional groups includes free radical-generating photoinitiators, optionally combined with a photosensitizer or accelerator. Such initiators typically can be capable of generating free radicals for addition polymerization upon exposure to light energy having a wavelength between about 400 and about 800 nm.
- a photoinitiation system can be selected from systems which initiate polymerization via a two component system of an amine and an a-diketone as described in US 4,071 ,424 and WO 2009151957, which are herein incorporated by reference.
- a typical example of such a system is the combination of camphorquinone and an amine.
- EDMAB ethyl 4-dimethylamino benzoate
- the resin can be combined with a three components or ternary photoinitiator system such as described in US 5,545,676 and WO 2009151957, which are incorporated herein by reference.
- the first component is an iodonium salt, i.e., a diaryliodonium salt.
- the iodonium salt is preferably soluble in the monomer and shelf-stable (i e., does not spontaneously promote polymerization) when dissolved therein in the presence of the sensitizer and donor. Accordingly, selection of a particular iodonium salt may depend to some extent upon the particular monomer, polymer or oligomer, sensitizer and donor chosen.
- iodonium salts are described in US 3,729,313, US 3,741 ,769, US 3,808,006, US 4,250,053 and US 4,394,403, the iodonium salt disclosures of which are incorporated herein by reference.
- the iodonium salt can be a simple salt (e.g., containing an anion such as CI “ , Br “ , I “ or C 4 H 5 S0 3 " ) or a metal complex salt (e.g., containing SbF 5 OH " or AsF 6 " ). Mixtures of iodonium salts can be used if desired.
- Preferred iodonium salts include diphenyliodonium salts such as diphenyliodonium chloride, diphenyliodonium hexafluorophosphate and diphenyliodonium tetrafluoroborate.
- the second component in a ternary photoinitiator system is a sensitizer.
- the sensitizer desirably is soluble in the monomer, and is capable of light absorption somewhere within the range of wavelengths of greater than 400 to 1200 nanometers, more preferably greater than 400 to 700 nanometers and most preferably greater than 400 to about 600 nanometers.
- the sensitizer may also be capable of sensitizing 2-methyl-4,6-bis(trichloromethyl)-s-triazine, using the test procedure described in US 3,729,313, which is incorporated herein by reference.
- a sensitizer is also selected based in part upon shelf stability considerations. Accordingly, selection of a particular sensitizer may depend to some extent upon the particular monomer, oligomer or polymer, iodonium salt and donor chosen.
- Suitable sensitizers can include compounds in the following categories: ketones, coumarin dyes (e.g., ketocoumarins), xanthene dyes, acridine dyes, thiazole dyes, thiazine dyes, oxazine dyes, azine dyes, aminoketone dyes, porphyrins, aromatic polycyclic hydrocarbons, p-substituted aminostyryl ketone compounds, aminotriaryl methanes, merocyanines, squarylium dyes and pyridinium dyes.
- ketones coumarin dyes (e.g., ketocoumarins), xanthene dyes, acridine dyes, thiazole dyes, thiazine dyes, oxazine dyes, azine dyes, aminoketone dyes, porphyrins, aromatic polycyclic hydrocarbons, p-substituted aminostyryl ketone compounds,
- Ketones e.g., monoketones or alpha-diketones
- ketocoumarins aminoarylketones
- p-substituted aminostyryl ketone compounds are preferred sensitizers.
- sensitizers having an extinction coefficient below about 1000, more preferably below about 100, at the desired wavelength of irradiation for photopolymerization.
- dyes that exhibit reduction in light absorption at the excitation wavelength upon irradiation can be used.
- a preferred class of ketone sensitizers has the formula: ACO(X) b B, where X is CO or CR 5 R 6 , where R 5 and R 6 can be the same or different, and can be hydrogen, alkyl, alkaryl or aralkyl, b is zero or one, and A and B different and can be substituted (having one or more non- interfering substituents) can be the same or unsubstituted aryl, alkyl, alkaryl, or aralkyl groups, or together A and B can form a cyclic structure which can be a substituted or unsubstituted cycloaliphatic, aromatic, heteroaromatic or fused aromatic ring.
- Suitable diketones include aralkyldiketones such as anthraquinone, phenanthrenequinone, o-, m- and p-diacetylbenzene, 1 ,3-, 1 ,4-, 1 ,5-, 1 ,6-, 1 ,7- and 1 ,8-diacetylnaphthalene, 1 ,5-, 1 ,8- and 9,10-diacetylanthracene, and the like.
- aralkyldiketones such as anthraquinone, phenanthrenequinone, o-, m- and p-diacetylbenzene, 1 ,3-, 1 ,4-, 1 ,5-, 1 ,6-, 1 ,7- and 1 ,8-diacetylnaphthalene, 1 ,5-, 1 ,8- and 9,10-diacetylanth
- Suitable alpha-diketones include 2,3-butanedione, 2,3-pentanedione, 2,3- hexanedione, 3,4-hexanedione, 2,3-heptanedione, 3,4-heptanedione, 2,3-octanedione, 4,5- octanedione, benzil, 2,2'- 3 3'- and 4,4'-dihydroxylbenzil, furil, di-3,3'-indolylethanedione, 2,3- bornanedione (camphorquinone), biacetyl, 1 ,2-cyclohexanedione, 1 ,2-naphthaquinone and the like.
- the third component of a ternary initiator system is a donor.
- Preferred donors include, for example, amines (including aminoaldehydes and aminosilanes), amides (including phosphoramides), ethers (including thioethers), ureas (including thioureas), ferrocene, sulfinic acids and their salts, salts of ferrocyanide, ascorbic acid and its salts, dithiocarbamic acid and its salts, salts of xanthates, salts of ethylene diamine tetraacetic acid and salts of tetraphenylboronic acid.
- the donor can be unsubstituted or substituted with one or more non- interfering substituents.
- Particularly preferred donors contain an electron donor atom such as a nitrogen, oxygen, phosphorus, or sulfur atom, and an abstractable hydrogen atom bonded to a carbon or silicon atom alpha to the electron donor atom.
- an electron donor atom such as a nitrogen, oxygen, phosphorus, or sulfur atom
- an abstractable hydrogen atom bonded to a carbon or silicon atom alpha to the electron donor atom.
- free-radical initiators useful in the invention include the class of acylphosphine oxides and bisacylphosphine oxides.
- Suitable acylphosphine oxides can be described by the general formula
- Preferred acylphosphine oxides are those in which the R 9 and R 10 groups are phenyl or lower alkyl- or lower alkoxy-substituted phenyl.
- R 9 and R 10 groups are phenyl or lower alkyl- or lower alkoxy-substituted phenyl.
- lower alkyl and lower alkoxy is meant such groups having from 1 to 4 carbon atoms. Examples can also be found e.g. in US 4,737,593.
- Suitable bisacylphosphine oxides can be described by the general formula
- R 4 , R 5 , R 6 and R 7 are H, C1-4 alkyl, C1-4 alkoxyl, F, CI or Br;
- R 2 and R 3 which are the same or different,stand for a cyclohexyl, cyclopentyl, phenyl, naphthyl, or biphenylyl radical, a cyclopentyl, cyclohexyl, phenyl, naphthyl, or biphenylyl radical substituted by F, CI, Br, I, C1-4 alkyl and/or C1-4 alkoxyl, or an S or N-containing 5-membered or 6- membered heterocyclic ring; or R 2 and R 3 are joined to form a ring containing from 4 to 10 carbon atoms and being optionally substituted by 1 to 6 C1-4 alkyl radicals.
- Further examples include: bis-(2,6-dichlorobenzoyl)phenylphosphine oxide, bis-(2,6- dichlorobenzoyl)-2,5-dimethylphenylphosphine oxide, bis-(2,6-dichlorobenzoyl)-4-ethoxy- phenylphosphine oxide, bis-(2,6-dichlorobenzoyl)-4-biphenylylphosphine oxide, bis-(2,6- dichlorobenzoyl)-4-propylphenylphosphine oxide, bis-(2,6-dichlorobenzoyl)-2-naphthyl- phosphine oxide, bis-(2,6-dichlorobenzoyl)-1 -napthylphosphine oxide, bis-(2,6-dichlorobenzoyl)- 4-chlorophenylphosphine oxide, bis-(2,6-dichlorobenzoyl)-2,4
- acylphosphine oxide bis(2,4,6-trimethylbenzoyl)phenyl phosphine oxide (IRGACURE 819, Ciba Specialty Chemicals, Tarrytown, NY) is sometimes preferred.
- Tertiary amine reducing agents may be used in combination with an acylphosphine oxide.
- Illustrative tertiary amines useful in the invention include ethyl 4-(N,N-dimethylamino)benzoate and ⁇ , ⁇ -dimethylaminoethyl methacrylate.
- phosphine oxide photoinitiators capable of free-radical initiation when irradiated at wavelengths of greater than 400 nm to 1200 nm include a 25:75 mixture, by weight, of bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentyl phosphine oxide and 2-hydroxy-2-methyl-1 - phenylpropan-1-one (IRGACURETM 1700, Ciba Specialty Chemicals), 2-benzyl-2-(N,N- dimethylamino)-1 -(4-morpholinophenyl)-1 -butanone (IRGACURETM 369, Ciba Specialty Chemicals), bis(n5-2,4-cyclopentadien-1 -yl)-bis(2,6-difluoro-3-(1 H-pyrrol-1 -yl)phenyl) titanium (IRGACURETM 784 DC, Ciba Specialty Chemicals), a 1 :1 mixture, by
- Useful amounts for photoinitiator system(s) include:
- Typical ranges include from about 0.1 wt.-% to about 5 wt.-% or from about 0.3 wt.-% to about 4 wt.-% or from about 0.5 wt.-% to about 3 wt.-%.
- the inventive composition may also comprise one or more non acid-reactive fillers as component (F) or part of component (F).
- a non-acid reactive filler is a filler which does not undergo an acid/base reaction with an acid.
- acid reactive fillers include certain fluoroalumina glasses (sometimes also referred to as GIZ glasses; those glasses typically have a weight ratio of AI203 to Si02 of at least 1 to 2, hydroxides, oxides and carbonates of alkaline earth metals like Ca(OH) 2, Mg(OH) 2, CaO, MgO, CaCOs, MgCOs.
- fluoroalumina glasses sometimes also referred to as GIZ glasses; those glasses typically have a weight ratio of AI203 to Si02 of at least 1 to 2, hydroxides, oxides and carbonates of alkaline earth metals like Ca(OH) 2, Mg(OH) 2, CaO, MgO, CaCOs, MgCOs.
- the inventive composition may comprise a filler or a filler matrix.
- the filler matrix can be comprised of one filler or a mixture of different fillers.
- filler of the inventive composition is not particularly limited provided the filler is non-acid reactive.
- the size of the filler particles should be such that a homogeneous mixture with the hardenable component(s) forming the resin matrix can be obtained.
- Useful fillers include fumed silica, fillers based on non-acid reactive fluoroaluminosilicate glasses, quartz, ground glasses, non-water-soluble fluorides such as CaF 2 , silica gels such as silicic acid, in particular pyrogenic silicic acid and granulates thereof, cristobalite, calcium silicate, zirconium silicate, zeolites, including molecular sieves.
- the silica is usually dispersed within the resin matrix.
- the silica particles used in the dental compositions preferably have an average diameter of less than about 200 nm or less than about 100 nm in average diameter. These measurements are preferably based on a TEM (transmission electron microscopy) method, whereby a population is analyzed to obtain an average particle diameter.
- a preferred method for measuring the particle diameter can be described is as follows:
- Samples approximately 80nm thick are placed on 200 mesh copper grids with carbon stabilized formvar substrates (SPI Supplies- a division of Structure Probe, Inc., West Chester, PA).
- a transmission electron micrograph (TEM) is taken, using JEOL 200CX (JEOL, Ltd. of Akishima, Japan and sold by JEOL USA, Inc.) at 200Kv.
- a population size of about 50-100 particles can be measured and an average diameter is determined.
- the average surface area of the silica particles is preferably greater than about 15 m 2 /g more preferably greater than about 30 m 2 /g.
- the silica particles are in a discrete (individual) and unassociated (i.e. non-agglomerated, non-aggregated) condition.
- Agglomerated as used herein, is descriptive of a weak association of particles usually held together by charge or polarity and can be broken down into smaller entities.
- Aggregated as used herein, is descriptive of a strong association of particles often bound together by, for example, residual chemicals treatment; further breakdown of the aggregates into smaller entities is very difficult to achieve.
- the silica particles which can be used in the dental materials of the invention are preferably substantially spherical and substantially non-porous. Although the silica is preferably essentially pure, it may contain small amounts of stabilizing ion such as ammonium and alkaline metal ions.
- Suitable fumed silicas include for example, products sold under the tradename AEROSIL series OX-50, -130, -150, and -200 available from Degussa AG, (Hanau, Germany), and CAB-O-SIL M5 available from Cabot Corp (Tuscola, III.).
- a heavy metal oxide or fluoride can be included in the dental materials of the invention to provide a radiopaque dental material. It is preferred that the heavy metal oxide or fluoride be present in an amount effective to impart radiopacity.
- radiopacity describes the ability of a hardened dental material to be distinguished from tooth structure using standard dental X-ray equipment in the conventional manner. Radiopacity in a dental material is advantageous in certain instances where X-rays are used to diagnose a dental condition. For example, a radiopaque material would allow the detection of secondary caries that may have formed in the tooth tissue surrounding a filling. The desired degree of radiopacity can be varied, depending upon the particular application and the expectations of the practitioner evaluating the X-ray film.
- Oxides or fluorides of heavy metals having an atomic number greater than about 28 can be preferred.
- the heavy metal oxide or fluoride should be chosen such that undesirable colors or shading are not imparted to the hardened resin in which it is dispersed. For example, iron and cobalt would not be favoured, as they impart dark and contrasting colors to the neutral tooth color of the dental material. More preferably, the heavy metal oxide or fluoride is an oxide or fluoride of metals having an atomic number greater than 30.
- Suitable metal oxides are the oxides of yttrium, strontium, barium, zirconium, hafnium, niobium, tantalum, tungsten, bismuth, molybdenum, tin, zinc, lanthanide elements (i.e. elements having atomic numbers ranging from 57 to 71 , inclusive), cerium and combinations thereof.
- Suitable metal fluorides are e.g. Yttriumtrifluoride and Ytterbiumtrifluoride. Most preferably, the oxides and fluorides of heavy metals having an atomic number greater than 30, but less than 72 are optionally included in the materials of the invention.
- radiopacifying metal oxides include lanthanum oxide, zirconium oxide, yttrium oxide, ytterbium oxide, , cerium oxide, and combinations thereof.
- the heavy metal oxide particles may be aggregated. If so, it is preferred that the aggregated particles are less than about 200 nm, and more preferably are less than about 90 nm in average diameter.
- Suitable fillers to increase radiopacity are salts of barium and strontium especially strontium sulphate and barium sulphate.
- the filler matrix comprises a nano-sized filler including nano-sized silica.
- Preferred nano-sized silicas are commercially available from Nalco Chemical Co. (Naperville, III.) under the product designation NALCO COLLOIDAL SILICAS (for example, preferred silica particles can be obtained from using NALCO products 1040, 1042, 1050, 1060, 2327 and 2329), Nissan Chemical America Company, Houston, Texas (for example, SNOWTEX-ZL, -OL, -O, -N, -C, -20L, -40, and -50); Admatechs Co., Ltd., Japan (for example, SX009-MIE, SX009- MIF, SC1050-MJM, and SC1050-MLV); Grace GmbH & Co.
- Surface-treating the nano-sized silica particles before loading into the dental material can provide a stable dispersion in the resin.
- “Stable”, as used herein, means a dental material in which the particles do not agglomerate after standing for a period of time, such as about 24 hours, under standard ambient conditions, e.g. room temperature (about 20 to about 22 °C), atmospheric pressure, and no extreme electromagnetic forces.
- the surface- treatment stabilizes the nano-sized particles so that the particles will be well dispersed in the hardenable resin and results in a substantially homogeneous composition.
- the silica be modified over at least a portion of its surface with a surface treatment agent so that the stabilized particle can copolymerize or otherwise react with the hardenable resin during curing.
- silica particles as well as other suitable non acid-reactive fillers according to the present invention can be treated with a resin-compatibilizing surface treatment agent.
- Particularly preferred surface treatment or surface modifying agents include silane treatment agents capable of polymerizing with a resin.
- Preferred silane treatment agent include ⁇ - methacryloxylpropyltrimethoxysilane, available commercially under the trade designation A-174, available commercially from Witco OSi Specialties (Danbury, Conn.) and ⁇ - glycidoxypropyltrimethoxy silane, a product available under the trade designation G6720, available from United Chemical Technologies (Bristol, Pa.).
- the polymerizing group can be ethylenically unsaturated or a cyclic function subject to ring opening polymerization.
- An ethylenically unsaturated polymerizing group can be, for example, an acrylate or methacrylate, or vinyl group.
- a cyclic functional group subject to ring opening polymerization generally contains a heteroatom such as oxygen, sulfur or nitrogen, and preferably is a 3-membered ring containing oxygen such as an epoxide.
- silane of this type include, for example, alkyl or aryl polyethers, alkyl, hydroxy alkyl, hydroxy aryl, or amino alkyl functional silanes.
- the silica particles Upon surface treating the silica particles, they can then be combined with an appropriate hardenable resin to form a dental composition of the invention.
- the filler(s) can also be based on an organic material.
- suitable organic filler particles include filled or unfilled pulverized polycarbonates, poly(meth)acrylates, polyepoxides, and the like.
- the amount of filler to be used in the filler matrix usually depends on the purpose for which the composition should be used.
- filler(s) Useful amounts for filler(s) include:
- Typical ranges include from about 0 wt.-% to about 90 wt.-% or from about from about 5 wt.-% to about 80 wt.-% or from about 10 wt.-% to about 70 wt.-%.
- the inventive composition may also comprise one or more additives as component (G) or part of component (G).
- Additives of adjuvants include accelerators, inhibitors or retarders, absorbers, stabilizers, pigments, dyes, surface tension depressants and wetting aids, antioxidants, and other ingredients well known to those skilled in the art.
- each ingredient in the composition should be adjusted to provide the desired physical and handling properties before and after polymerization.
- dyes or pigments examples include titanium dioxide or zinc sulphide (lithopones), red iron oxide 3395, Bayferrox 920 Z Yellow, Neazopon Blue 807 (copper phthalocyanine-based dye) or Helio Fast Yellow ER. These additives may be used for individual colouring of the dental compositions.
- photobleachable colorants which can be present include Rose Bengal, Methylene Violet, Methylene Blue, Fluorescein, Eosin Yellow, Eosin Y, Ethyl Eosin, Eosin bluish, Eosin B, Erythrosin B, Erythrosin Yellowish Blend, Toluidine Blue, 4',5'-Dibromofluorescein and blends thereof. Further examples of photobleachable colorants can be found in US 6,444,725.
- the colour of the compositions of the invention may be additionally imparted by a sensitizing compound.
- fluoride release agents which can be present include naturally occuring or synthetic fluoride minerals. These fluoride sources can optionally be treated with surface treatment agents.
- stabilizers especially free radical scavengers such as substituted and/or unsubstituted hydroxyaromatics (e.g. butylated hydroxytoluene (BHT), hydroquinone, hydroquinone monomethyl ether (MEHQ), 3,5-di-tert-butyl-4- hydroxyanisole (2,6-di-tert-butyl-4-ethoxyphenol), 2,6-di-tert-butyl-4-(dimethylamino)methyl- phenol or 2,5-di-tert-butyl hydroquinone, 2-(2'-hydroxy-5'-methylphenyl)-2H-benzotriazole, 2-(2'- hydroxy-5'-t-octylphenyl)-2H-benzotriazole, 2-hydroxy-4-methoxybenzophenone (UV-9), 2-(2'- hydroxy-4',6'-di-tert-pentylphenyl)
- BHT butylated hydroxy
- retarders such as 1 ,2-diphenylethylene
- plasticizers including polyethylene glycol derivatives, polypropylene glycols, low-molecular- weight polyesters, dibutyl, dioctyl, dinonyl and diphenyl phthalate, di(isononyl adipate), tricresyl phosphate, paraffin oils, glycerol triacetate, bisphenol A diacetate, ethoxylated bisphenol A diacetate, and silicone oils
- flavorants anti-microbials
- fragrance agents that impart fluorescence and/or opalescence and fluoride releasing materials.
- soluble organic polymers including polyvinyl acetate, and copolymers thereof.
- adjuvants or additives there is no absolute need for these adjuvants or additives to be present, so adjuvants or additives might not be present at all. However, if they are present they are typically present in an amount which is not detrimental to the intended purpose.
- Useful amounts for additives include:
- Typical ranges include from about 0 wt.-% to about 15 wt.-% or from about from about 0.5 wt.-% to about 10 wt.-% or from about 1 wt.-% to about 5 wt.-%.
- the curable composition of the invention can be obtained by combining (including mixing and kneading) the individual components of the composition, preferably under "safe light” conditions.
- Suitable inert solvents may be employed if desired when providing the mixture. Any solvent may be used which does not react appreciably with the components of the inventive compositions.
- solvents include, but are not limited to linear, branched or cyclic, saturated or unsaturated alcohols, ketones, esters or mixtures of two or more of said type of solvents with 2 to 10 C atoms.
- Preferred alcoholic solvents include methanol, ethanol, iso-propanol and n- propanol.
- organic solvents are THF, acetone, methylethyl ketone, cyclohexanol, toluene, alkanes and acetic acid alkyl esters, in particular acetic acid ethyl ester.
- compositions of the invention are particularly well adapted for use as a wide variety of dental materials, which may be filled or unfilled.
- Such dental materials include direct aesthetic restorative materials (e.g., anterior and posterior restoratives), adhesives and primers for oral hard tissues, sealants, cavity liners, orthodontic bracket adhesives for use with any type of bracket (such as metal, plastic and ceramic), crown and bridge cements, and the like. These dental materials are used in the mouth and are disposed adjacent to natural teeth.
- the phrase "disposed adjacent to” as used herein refers to the placing of a dental material in temporary or permanent bonding (e.g., adhesive) or touching (e.g., occlusal or proximal) contact with a natural tooth.
- composite as used herein in the context of a dental material refers to a filled dental material.
- restorative refers to a dental composite that is polymerized after it is disposed adjacent to a tooth.
- prosthesis refers to a composite that is shaped and polymerized for its final use (e.g., as a crown, bridge, veneer, inlay, onlay or the like) before it is disposed adjacent to a tooth.
- silant refers to a lightly filled dental composite or to an unfilled dental material that is cured after it is disposed adjacent to a tooth.
- the tooth can optionally be pre-treated with a primer such as a dentin or enamel adhesive by methods known to those skilled in the art.
- inventive composition in the dental field include the use as anterior or posterior filling, adhesive, cavity liner, flowable, cement, coating composition, root canal filler, root canal sealant or core build-up material.
- a typical application process for the inventive composition typically includes the following steps in the desired order:
- the composition is either dispensed from a compule (typically used for single applications) or from a vessel or screw tube (typically used for multiple applications).
- composition is self-adhesive, no prior etching step or use of a bonding/primer is needed.
- the inventive composition is typically stored in a container until use.
- the composition described in the present text is stored in only one compartment of the container.
- the composition is not separated into different parts and stored in different compartments of the container.
- a one-component system can be stored in a container having only one chamber such as a compule or a screw tube or a syringe.
- the compule has typically a cylindrical housing with a front and a rear end and a nozzle. The rear end of the housing is usually sealed with a movable piston.
- the dental composition is dispensed out of the compule or container using an applier having a movable plunger (e.g. an application device having the shape of a caulk gun).
- the volume of the container is typically in the range from about 0.1 to about 100 ml or from about 0.5 to about 50 ml or from about 1 to about 30 ml.
- the inventive composition does typically not contain acid- reactive, basic fillers like the oxides, carbonates and hydroxides of calcium, magnesium, strontium, zinc, acid-reactive fluoroaluminosilicate glasses or mixtures thereof, especially fillers which are able to react with the acidic components of the inventive composition in an ion exchange, neutralization, salt-forming and/or chelate-forming reaction.
- acid- reactive, basic fillers like the oxides, carbonates and hydroxides of calcium, magnesium, strontium, zinc, acid-reactive fluoroaluminosilicate glasses or mixtures thereof, especially fillers which are able to react with the acidic components of the inventive composition in an ion exchange, neutralization, salt-forming and/or chelate-forming reaction.
- fillers can, however, be present in neutralized form, that is, in a form where the filler(s) has(have) already reacted with the acidic component(s) of the composition and thus do(es) not jeopardize the etching and/or self-adhesive properties of the inventive composition.
- the pH value of the final composition should, however, still be in a range from about 0 to 5 or 1 to 4.
- a basic filler might negatively affect the adhesion properties due to a neutralization reaction with the monomers comprising an acidic moiety.
- monomers comprising acidic moieties are typically required to etch the surface of the tooth to be treated and to make a composition self-adhering to dental surfaces.
- the inventive composition does typically (also) not contain components comprising a sulfinate moiety (especially sulfinate salts such as sodium toluene sulfinate), barbituric acid moiety, thiobarbituric acid moiety, an aryl borate moiety or mixtures thereof.
- a sulfinate moiety especially sulfinate salts such as sodium toluene sulfinate
- barbituric acid moiety especially thiobarbituric acid moiety, an aryl borate moiety or mixtures thereof.
- inventive composition may not comprise either of the following combinations of components:
- component comprising an aryl borate moiety and component comprising a sulfinate moiety.
- aryl borate moiety and component comprising a sulfinate moiety.
- sulfinate moiety unavoidable traces of these components might be present (e.g. due to impurities in the raw materials used). However, those components are typically not willfully added in an amount to participate in the curing reaction.
- UDMA 7,7,9-(resp. 7,9,9-)Trimethyl-4, 13-dioxo-3, 14-dioxa-5, 12-diaza-hexadecane-1 , 16- dioxy dimethacrylate (mixture of isomers)
- GDMP Glycerol dimethacrylate phosphate
- HDK H-2000 Fumed silica
- SABS I Strontiumaluminoborosilicate glass filler, 3% silane treated
- SABS II Strontiumaluminoborosilicate glass filler, 4.6% silane treated
- Na-Persulphate Na-peroxodisulphate / strontiumaluminoborosilicate glass filler (Mixture
- Formulations including urethane(meth)acrylate and GDMP with and without copper salt and persulphate compound (Table 2).
- Tables 3 and 4 demonstrate that formulations according to the invention with a persulphate and a copper compound (Example 1 and 2) result in good mechanical and adhesion performance, especially with respect to dentin surfaces. Omitting persulphate (Comparative Example 1 and 4) or copper (Comparative Example 3) or both components (Comparative Example 2 and 5) results in a significantly lower adhesion to dentin.
- the commercially available product VertiseTM Flow (Kerr) also revealed significantly lower adhesion to dentin.
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Abstract
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EP12798129.8A EP2785307B1 (fr) | 2011-12-01 | 2012-11-30 | Composition dentaire autoadhésive à un composant, son procédé de fabrication et son utilisation |
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EP11191541 | 2011-12-01 | ||
PCT/US2012/067159 WO2013082337A1 (fr) | 2011-12-01 | 2012-11-30 | Composition dentaire autoadhésive à un composant, son procédé de fabrication et son utilisation |
EP12798129.8A EP2785307B1 (fr) | 2011-12-01 | 2012-11-30 | Composition dentaire autoadhésive à un composant, son procédé de fabrication et son utilisation |
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CN106029045B (zh) * | 2014-02-18 | 2020-04-03 | 3M创新有限公司 | 牙科组合物及其用途 |
CN106029046B (zh) * | 2014-02-18 | 2019-04-05 | 3M创新有限公司 | 牙科用组合物及其用途 |
US9844493B2 (en) * | 2014-02-18 | 2017-12-19 | 3M Innovative Properties Company | Adhesive bonding composition and use thereof |
CN104592927B (zh) * | 2015-02-09 | 2017-02-22 | 哈尔滨理工大学 | 一种点胶纸用水溶性粘合剂的制备方法 |
EP3153756B1 (fr) * | 2015-10-08 | 2020-05-06 | Crompton Technology Group Limited | Isolateur électrique |
US10617607B2 (en) | 2015-11-06 | 2020-04-14 | 3M Innovative Properties Company | Redox polymerizable dental composition with photolabile transition metal complexes |
CN108348403B (zh) * | 2015-11-06 | 2021-06-18 | 3M创新有限公司 | 含有光不稳定过渡金属络合物的氧化还原可聚合组合物 |
CN108366911A (zh) * | 2015-12-08 | 2018-08-03 | 3M创新有限公司 | 两组分自粘合牙科用组合物,储存稳定的引发剂体系以及它们的用途 |
US10987281B2 (en) | 2016-10-21 | 2021-04-27 | Kuraray Noritake Dental Inc. | Self-adhesive dental composite resin |
CN106726623B (zh) * | 2016-12-28 | 2020-12-04 | 日照沪鸽生物材料有限公司 | 用于牙体修复具有氟离子释放特性的单组分光固化复合材料及其应用 |
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- 2012-11-30 BR BR112014013111A patent/BR112014013111A2/pt not_active Application Discontinuation
- 2012-11-30 JP JP2014544899A patent/JP6139551B2/ja active Active
- 2012-11-30 CN CN201280059074.1A patent/CN104114142B/zh active Active
- 2012-11-30 RU RU2014121153/15A patent/RU2600814C2/ru not_active IP Right Cessation
- 2012-11-30 WO PCT/US2012/067159 patent/WO2013082337A1/fr active Application Filing
- 2012-11-30 EP EP12798129.8A patent/EP2785307B1/fr active Active
- 2012-11-30 US US14/360,373 patent/US9132069B2/en active Active
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Also Published As
Publication number | Publication date |
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CN104114142A (zh) | 2014-10-22 |
EP2785307B1 (fr) | 2019-06-26 |
BR112014013111A2 (pt) | 2017-06-13 |
US9132069B2 (en) | 2015-09-15 |
RU2600814C2 (ru) | 2016-10-27 |
US20140329205A1 (en) | 2014-11-06 |
WO2013082337A1 (fr) | 2013-06-06 |
JP6139551B2 (ja) | 2017-05-31 |
JP2015507610A (ja) | 2015-03-12 |
RU2014121153A (ru) | 2016-02-10 |
CN104114142B (zh) | 2016-12-21 |
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